


Bright Red Heels

by hurluberlu



Category: Supernatural
Genre: Alternate Universe - Office, Business AU, Crossdressing, Dubious Consent, M/M, Smut, Transgender, Workplace Sex
Language: English
Status: Completed
Published: 2015-07-09
Updated: 2015-07-09
Packaged: 2018-04-08 10:39:45
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,108
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4301589
Author URL: https://archiveofourown.org/users/hurluberlu/pseuds/hurluberlu
Summary: <blockquote class="userstuff">
              <p>"I'm clearly attracted to dudes, but that doesn't make me gay if I'm a woman."</p><p>"So you don't want to be gay?"</p><p>"I don't want to be a <i>guy</i>."</p>
            </blockquote>





	Bright Red Heels

"So that's an interesting outfit." Sam said as he looked down at his best friend.

Cas smiled and laughed, placing his fingertips at the hem of his dress and doing a fake curtsy in his office chair.

"What can I say? I felt pretty this morning."

Sam laughed and placed a hand on his hip. Extending the other to the man in front of him, wearing a tight black dress that only went down the middle of his thighs, Sam smirked and did a small bow.

"May I escort you to the lunch room, Ms. Castiel?"

Cas laughed louder, playing along as he delicately placed his hand into Sam's.

"Well that would be just lovely."

Castiel stood up from his chair, locking arms with Sam as he was led to the break room. The steady sound of his heels was the loudest noise in the office, aside from the occasional laugh as he walked through the halls confidently.

Sam unhooked his arm from Castiel's, stepping in front of him to pull out a chair. Castiel smiled and sat down, watching as Sam grabbed a bag and a water bottle from the refrigerator before sitting across from him.

"So really, why are you wearing that?" Sam asked as he pulled a bag of pretzels out of his lunch bag and threw them to Cas.

Castiel caught the pretzels and opened the bag, placing one in his mouth. He slowly chewed the pretzel, trying to avoid the question. He reached for the water bottle, sighing when Sam grabbed it and held it in his lap.

"Not until I get an answer."

Castiel pouted and crossed his arms over his chest.

"Oh come onnnn. I'm curious. There has to be a reason."

Castiel placed his arms on the table and grabbed the pretzel bag.

"What if there isn't a real reason?"

Sam laughed and opened the water bottle, taking a sip before returning it to his lap.

"Just tell me Cas."

Castiel shook his head and ate a second pretzel. He looked over the table to where he could see the lid of the bottle in Sam's hands.

"I'm not afraid to try and grab that you know."

Sam nodded and lifted the bottle up, placing it back on the table.

"Come on Cas, just tell meee..."

Castiel sighed and took the bottle, unscrewing the cap and taking a sip.

"Mr. Winchester."

Sam tilted his head in confusion.

"You're wearing it for Mr. Winchester?"

Castiel nodded, feeling his cheeks get slightly red.

"I've got it bad Sam."

Cas put his hands on his cheeks, placing his elbows on the table.

"Do you remember last week, when we had the performance meeting?"

Sam nodded, waiting for Castiel to continue.

"And when Mr. Winchester placed his hand on my shoulder and complimented my sales numbers?"

Sam nodded again. "Vaguely, yes."

"I swear to you I almost got a hard-on."

Sam's eyes widened and he grabbed the water bottle again, taking a sip.

"Jesus Christ Cas."

Castiel closed his eyes and rubbed his forehead.

"Just thinking about it even makes me just so-"

"I don't wanna know Cas."

Castiel smiled and reopened his eyes.

"So how is dressing like that supposed to do anything about it?"

Castiel glanced at the clock, and seeing they only had about three minutes left for their lunch break, he looked back at Sam.

"Do you really want to know?"

Sam quickly shook his head and grabbed his uneaten lunch, standing up to put it back in the fridge.

"Probably not."

Castiel stood up, grabbing the empty bottle and throwing it into the recycling bin, before coming back to grab the pretzels. Sam followed Castiel to the trash can as Castiel threw away the pretzels. He glanced down at Castiel's heels, bright red, then let his eyes trail up the back of Castiel's hairless legs.

"I do have to say, you look incredibly hot in that dress."

Castiel laughed and grabbed Sam's arm.

"Not interested."

Sam led Castiel back to his desk, watching as Castiel sat down in his chair and laid his head on the headrest.

Sam closed his eyes and covered his face. "Oh god Cas."

Castiel lifted his head.

"What's wrong?"

Sam opened his eyes and moved his fingers so he could look through his hands.

"Look down."

Castiel looked down. "Shit!"

Cas quickly grabbed the hem of his dress, trying to pull it down, as it was just short enough to show the head of his penis.

Sam removed his hands from his face as he saw Cas's face get bright red.

"Sorry Sam."

Sam smiled awkwardly and looked up to see Mr. Winchester walking towards Castiel's desk.

"I think someone told Mr. Winchester about your outfit, he's making a beeline towards your desk."

Castiel's face lit up, and just before Mr. Winchester made it to his desk, Sam had said 'Good luck' and walked away.

Mr. Winchester placed a hand on Castiel's cubicle's wall.

"Mr. Novak, could you come to my office?"

Castiel took a deep breath, before putting on a face of innocence and turning around in his chair.

"Uh sure."

Mr. Winchester smiled and waited for Castiel to stand up before walking back to his office. He opened the door, holding it for Castiel before softly closing it behind him.

"Please take a seat." Mr. Winchester said, gesturing to the chair across from his own. Castiel nodded and sat down, before watching Mr. Winchester take his seat.

"I imagine you know why I called you into my office."

Castiel nodded and looked down to his dress, slipping it up slightly so his cock was barely visible.

Mr. Winchester stood from his seat walking to a cabinet in the corner of his office.

"Do you have any clothes to change into that are more...appropriate?"

Castiel shook his head, still feigning innocence.

Mr. Winchester opened a drawer, taking out a pair of jeans and button-up shirt.

"I imagine we might be around the same size so you could go into the bathroom and put these on," Mr. Winchester brought the clothing to his desk, placing them in front of Castiel, "and please, pull down your dress until then."

Castiel looked up into Mr. Winchester's eyes, his own starting to show his mischief.

Castiel pulled his dress down, watching as Mr. Winchester walked around his desk and sat back down. Castiel put a hand on the clothes, before bringing a knee up to climb onto the desk and sit down, facing Mr. Winchester with his legs crossed.

"What if I don't want to?"

Mr. Winchester stood up, grabbing the clothes from behind Castiel, placing his chest flat against Castiel's in the process. Mr. Winchester refolded the clothing, placing it on Castiel's lap before sitting down again.

"Then I'll have to send you home early."

Castiel pouted, opening his legs, making the clothes fall to the floor and his dress ride up, fully exposing his half-hard penis.

Mr. Winchester closed his eyes, standing from his chair before reopening them to look directly into Castiel's.

"Mr. Novak, close your legs, stand up, and walk out of this building and I will consider not reporting this."

Castiel frowned, grabbing Mr. Winchester's hand and placing it over his cock before Mr. Winchester pulled his hand away forcefully.

"Come on Dean, have a little fun. I dressed like this for you."

Dean shook his head and grabbed Castiel's shoulders, pulling him of off the desk.

"Well I'm not interested Mr. Novak. And you are my employee, you will call me Mr. Winchester."

Castiel dropped to his knees when Dean let go of his shoulders and smiled up at his stern face.

"God Dean, you're dominance is so fucking hot."

Mr. Winchester sighed angrily and walked to his door, opening it before walking into the hall, leaving Castiel on the floor. Castiel looked down at himself, a feeling of shame flooding over him. He slowly stood up, taking off his heels and pulling down his dress trying to hide his obvious erection.

As Castiel was walking towards the door, tears threatening to fall, he looked up to see Mr. Winchester opening the door and rushing back in.

"I'm-I'm sorry, I was just leaving-"

Castiel almost fell backwards when Dean grabbed his face, bringing him into a one-sided kiss.

Dean pulled away, looking over Castiel's face, slightly damp from tears and bright red with surprise.

"Damn it Mr. Novak."

Dean pulled Castiel back in, waiting for Castiel to react.

Castiel opened his mouth hungrily allowing Dean's tongue inside. Castiel moaned, bringing a hand underneath of his dress, curling his fingers around his cock, now leaking precum.

Mr. Winchester grabbed Castiel's hand, stopping it's motion and pulling it out of Castiel's dress, still locked in the kiss. Dean put his hands on the back of Castiel's thighs, slowly moving them upward to push his dress up, revealing his ass.

Dean put his hands back down on Cas's thighs, picking Castiel up and sitting him on his desk. Dean finally broke the kiss, looking down at Cas's fully exposed erection.

"Fuck. I shouldn't be doing this."

Castiel leaned forward, gently sucking on Dean's neck just underneath his jawline, leaving a bruise that would no doubt be there for days.

"Mr. Novak, I have a wife. A child. I can't..."

Castiel pulled away. "Can't what? Have sex with me? Be 'gay'?" Cas looked down at Mr. Winchester's growing bulge. "Because that's not what your hard cock is telling me."

Dean took a few steps back, running his hand through his hair. "I'm sorry Mr. Novak, I can't go through with this."

Castiel stood from the desk pulling his dress over his head, revealing a toned torso and a single nipple piercing. "Are you sure?"

Dean's breath hitched and his voice faltered. "No..."

Castiel stepped forward, and Dean stood still in the middle of his office as Cas approached. Castiel reached his hands out to loosen Dean's tie, then unbuttoned the first few buttons on his shirt.

A knock on the door made him swat away Castiel's hands.

"Hide under my desk."

Castiel shook his head and took a step towards the door, and Dean's hand flew out to stop him.

"Damn it Castiel, listen to me! I can't open the door with a naked man standing in the middle of my office! Hide under the goddamn desk!"

Castiel wordlessly obeyed, crawling under the desk and pressing a ear to the back panel.

Dean sighed and opened the door, tie falling off, shirt slightly unbuttoned, hair in a mess and the bulge in his jeans very visible.

Bobby looked Dean up and down, then looked into the office, seeing the discarded dress and heels. He laughed to himself before looking back at Dean's face.

"I'm guessing I interrupted something?"

Dean looked back at the dress and heels and cursed under his breath.

"Uh, yeah."

Bobby shook his head.

"Damn it Dean, you have a beautiful wife at home."

Dean sighed and nodded. "I know Bobby. But you have to promise to me you will not tell her."

"It's not my place to tell her."

Castiel silently listened to the conversation, resisting the urge to crawl out and tell Bobby to 'fuck off'.

Bobby took another look into the office. "This better be over with before four, you have another performance meeting."

Dean nodded and smiled weakly. "Okay Bobby."

Bobby walked away from Dean's office, entering his own a few rooms over.

Dean closed the door, feeling more guilt about his wife.

Castiel crawled out from under the desk and stood up. He sighed and grabbed his heels, slipping them on.

"Let me guess, you can't do it?"

Dean looked over to Castiel, who was bent over, picking up his dress.

"Why did you wear it?"

Castiel stood up, about to slip the dress back on before Dean grabbed his arm, stopping him.

"Isn't it obvious Mr. Winchester? You're so fucking hot, I've dreamed of having your cock inside of me, splitting me open, your cum filling my insides-"

Dean closed his eyes and shook his head. "No, I mean why did you wear a dress and heels?"

Castiel looked down at the black fabric in his hands. "Because it makes me feel...good. Sexy. And feminine."

"Why do you want to be feminine?"

Castiel tilted his head and let out a sarcastic laugh. He gestured down to his erect cock. "I'm clearly attracted to dudes, but that doesn't make me gay if I'm a woman."

Dean took a step forward, placing a hand on Castiel's shoulder. "So you don't want to be gay?"

"I don't want to be a _guy_."

Castiel looked down at the floor, exhaling loudly. "I don't feel like talking about my problems, can you just tell if we're going to have sex?"

Dean took off his suit jacket, letting it fall to the floor before he slipped off his tie and finished unbuttoning his shirt. Castiel smiled, walking over to Mr. Winchester.

He fell to his knees, quickly undoing Mr. Winchester's belt and sliding his pants down to his feet. Castiel smirked, looking directly into Dean's eyes, before turning his attention to Dean's slowly dampening boxers.

Cas leaned forward, placing his lips over Dean's clothed cock, licking softly as Dean's knees buckled.

"You-you don't have to do that."

Castiel pulled away, only to pull down Dean's boxers, a spark running through his body at the sight of Dean's throbbing penis.

"Trust me, I want to."

Dean watched as Cas's tongue licked his entire length, from his balls to his leaking head. Castiel placed his hands on Dean's thighs as his mouth circled the base of Dean's penis.

Dean moaned every time Castiel's tongue brushed his testicles, and he gasped every time Castiel's tongue flicked softly over his slit.

Castiel pulled away, standing up so he could hook his arms around Dean's neck. He stood on his tiptoes, placing his mouth over Dean's ear.

"Fuck me Mr. Winchester."

Dean placed his arms around Castiel's waist, picking him up as Castiel hooked his legs around Dean's hips. Castiel watched as Dean tried to clean off his desk with one hand, and then tried to pick his computer monitor up.

Castiel moved his hips upwards, getting Dean's attention as their heads rubbed together. "Jesus Christ, just fuck me on the floor."

Dean looked down at the man who was desperately humping him. He wordlessly obliged, laying Cas down on the floor, placing his hands on either side of Castiel's head.

"Don't you need to prepare?"

Castiel nodded before he reached up to grab his dress. He reached into the neckline, grabbing a small container he held there with a safety pin. Dean subconsciously glanced up at the clock, cursing under his breath when he saw the time: 3:58.

"Shit Castiel, we only have two minutes."

Castiel quickly opened the lubricant container, carelessly squirting the liquid onto his fingers. He reached down in between his legs, using his other hand to give the lubricant to Dean.

"Put some on your penis."

Dean nodded, squeezing the bottle and coating his cock with the cold liquid. He watched as Castiel slipped a finger into his ass, biting his lip to hide the pain. He quickly inserted a second, then a third, trying to speed up the process.

Cas removed his fingers, looking down at Dean, who was staring hungrily back at him. "I'm ready."

"Are you sure?"

Castiel laid his thighs flat on the ground, answering Dean's question without words.

Dean grabbed Castiel's hips, gently nudging his cock against Castiel's ass. Castiel took a deep breath as Dean started to slowly push into him. Dean watched Castiel's face, slowing even more when he saw it contort in pain.

"Do I need to pull out?"

Castiel laid his head on the floor, stretching his neck upward and digging his nails into the carpet.

"Fuck no!"

Dean felt Castiel cover his hands that were still on Castiel's hips. 

"Keep going." 

Dean thrust deeper, hearing Castiel's breath hitch as he hit Castiel's prostate. Dean smiled, pulling out a small bit, before quickly thrusting back in, hitting Castiel's prostate directly. Castiel immediately tightened around him, breathing heavily as his orgasm approached.

Dean cursed when he heard a knock on the door. He looked up at the clock: 4:08.

Dean glanced between the man beneath him and the door, trying to decide which to prioritize. As he listened to the whimpers escaping Castiel's mouth, he brought his attention back to Castiel.

He thrust into Castiel roughly, hearing the door open mere seconds before Castiel reached his orgasm.

As cum sprayed between the two men's stomachs, the door was quickly slammed shut. Dean shot cum deep inside of Castiel, collapsing onto his stomach as they both struggled to catch their breaths.

Dean pulled out of Castiel, standing up and reaching a hand out to help Cas up. Castiel took his hand, grabbing his dress before he stood up to put it back on.

As Dean put his suit on piece by piece, deciding to forget about his tie, he stared at the door to make sure it wasn't opened again.

Castiel pulled the dress over his head, smearing the cum down the inside, invisible from the outside. He slipped on his heels at the same time Dean walked over to his mirror to fix his hair.

"Who was at the door?"

Dean shook his head.

"I don't know."

Dean slowly walked to the door, opening it. He was pushed back into the room and the door was roughly shut.

"What the hell Dean? I told you four, and it's almost 4:10!"

Bobby looked behind Dean, seeing the dress and heels now on a person. 

"And it was a dude!"

Dean took a step backwards, holding his arm out, trying to shield Castiel.

"Look Bobby, for all intents and purposes, Mr. Novak is a woman. And Jesus Christ, the meeting can wait ten minutes."

Bobby shook his head and pointed to the door. 

"You both better get your asses to that meeting, and if you two say anything about what happened between you two, Mr. Novak you will not have a job."

Bobby stormed out of the room, heading straight for the meeting room.

Dean pointed to the door. "You should go first, tell them you were in the bathroom. I'll go grab a coffee and say that's why I'm late."

Castiel nodded, and Dean listened to his heels go down the hallway until he couldn't hear them.

Dean turned to the nearest wall and hit his head against it.

"Fuck."


End file.
